Synthesis 2005(5): 741-748  
DOI: 10.1055/s-2005-861795
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Characterization of Several Soluble Tetraphenoxy-Substituted Copper and Zinc Phthalocyanines

Chunyu Maa, Dongliang Tianc, Xiaoke Houb, Yuchun Changa,b, Fangdi Congc, Haifeng Yuc, Xiguang Du*c, Guotong Du*a,b
a Department of Physics, Dalian University of Technology, Dalian 116023, P. R. China
Fax: +86(411)4709304; e-Mail: bandaoti@mail.dlut.edu.cn; e-Mail: chunyu3ma76@yahoo.com.cn;
b State Key Laboratory of Integrated Optoelectronics, Jilin University, Changchun 130021, P. R. China
c Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China
Further Information

Publication History

Received 18 October 2004
Publication Date:
09 February 2005 (online)

Abstract

Synthesis of copper and zinc phthalocyanines (Pcs) bearing phenoxy-substituents is described. Precursors required for the preparation of Pcs 9-16 are prepared by a nucleophilic aromatic substitution reaction between a sterically hindered phenol derivative and 4-nitrophthalonitrile (1) or 3-nitrophthalonitrile (2). Cyclotetramerization of the resulting precursor phthalonitriles in DMAE or in pentan-1-ol catalyzed by DBU gives desired Pcs, which are well soluble in common organic solvents, such as chloroform and dichloromethane. Each of these Pcs are composed of four constitutional isomers and are characterized by 1H NMR, UV/Vis, IR and mass spectra, as well as elemental analysis, which are consistent with the proposed structures.